Diisopropylamine → 4-Fluoro-3-methyl-5-(tributylstannyl)pyridine

HRID 2069094Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2069094
C(NC(C)C)(C)C.C([Li])CCC.[F:13][C:14]1[CH:19]=[CH:18][N:17]=[CH:16][C:15]=1[CH3:20].[CH2:21]([Sn:25](Cl)([CH2:30][CH2:31][CH2:32][CH3:33])[CH2:26][CH2:27][CH2:28][CH3:29])[CH2:22][CH2:23][CH3:24].C(=O)(O)[O-].[Na+]>C1COCC1>[F:13][C:14]1[C:19]([Sn:25]([CH2:26][CH2:27][CH2:28][CH3:29])([CH2:30][CH2:31][CH2:32][CH3:33])[CH2:21][CH2:22][CH2:23][CH3:24])=[CH:18][N:17]=[CH:16][C:15]=1[CH3:20]

Komponenten

7

Edukt 5

HCID 7912DiisopropylamineHCID 15096Tributyltin ChlorideHCID 516892Sodium BicarbonateHCID 27629214-Fluoro-3-methylpyridineHCID 178418339Butyllithium

Produkt 1

HCID 595351114-Fluoro-3-methyl-5-(tributylstannyl)pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A THF (1 mL) solution of diisopropylamine (160 μL; WAKO) was cooled to −78° C. under a nitrogen atmosphere followed by the dropwise addition of normal butyllithium (2.6 M, 430 μL; KANTO). The resulting mixture was stirred as it was for 30 minutes followed by the dropwise addition of a THF (1 mL) solution of 4-fluoro-3-methylpyridine (111 mg) and the resulting mixture was further stirred for 1 hour. Then tri-n-butyltin chloride (330 μL; TCI) was added and the resulting mixture was slowly raised to room temperature and then stirred for 2 hours. Saturated aqueous sodium bicarbonate solution was added to the reaction mixture solution, to the reaction mixture was extracted with ethyl acetate, and the organic layer was washed with saturated brine. The organic layer was dried and the solvent was evaporated under reduced pressure to give the title compound.

Aufarbeitung

  1. stirringthe resulting mixture was further stirred for 1 hour
  2. stirringstirred for 2 hours
  3. extractionwas extracted with ethyl acetate
  4. washthe organic layer was washed with saturated brine
  5. customThe organic layer was dried
  6. customthe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ec39fc47cccd4e13b10468c81d75859a
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08299055B2

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